The Chaplin Estates neighbourhood began with a plan of subdivision, registered by William John Chaplin and his son James D. Chaplin, in 1913. The Chaplin family had been landowners in this area dating back to 1860, when this district was known simply as 'Eglinton'. 

Chaplin Estates was marketed as a high class residential district. The developers included a long list of building restrictions and zoning bylaws, in the sale of each property. There were no semi-detached houses allowed, and stucco exteriors were not to cover more than half the house.

The marketing of the subdivision was handled by the Chaplin Realty Company. Prices ranged from $500 to $9,000 a lot. Most of the lots were sold between 1921 and 1925.